TY  - JOUR
A1  - Mahl, Magnus
A1  - Shoyama, Kazutaka
A1  - Krause, Ana‐Maria
A1  - Schmidt, David
A1  - Würthner, Frank
T1  - Base‐Assisted Imidization: A Synthetic Method for the Introduction of Bulky Imide Substituents to Control Packing and Optical Properties of Naphthalene and Perylene Imides
JF  - Angewandte Chemie International Edition
N2  - We report the direct imidization of naphthalene and perylene dicarboxylic anhydrides/esters with bulky ortho,ortho‐diaryl‐ and ortho,ortho‐dialkynylaniline derivatives. This imidization method uses n‐butyllithium as a strong base to increase the reactivity of bulky amine derivatives, proceeds under mild reaction conditions, requires only stoichiometric amounts of reactants and gives straightforward access to new sterically crowded rylene dicarboximides. Mechanistic investigations suggest an isoimide as intermediary product, which was converted to the corresponding imide upon addition of an aqueous base. Single‐crystal X‐ray diffraction analyses reveal dimeric packing motifs for monoimides, while two‐side shielded bisimides crystallize in isolated molecules without close π–π‐interactions. Spectroscopic investigations disclose the influence of the bulky substituents on the optical properties in the solid state.
KW  - dyes
KW  - fluorescence
KW  - imidization
KW  - perylene imide
KW  - solid-state emitters
Y1  - 2020
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-218246
VL  - 59
IS  - 32
SP  - 13401
EP  - 13405
ER  -